Middletown, NY Homes for Sale under $400,000

This beautifully updated Cape Cod–style single-family home offers 3 bedrooms and 2.5 baths, including a generous first-floor primary suite. The main level features a spacious living room with a fireplace, a formal dining room, and an elegant kitchen with granite and wood countertops along with stainless steel appliances. High ceilings, detailed moldings, a full bath, and a convenient laundry area

Jonathon Lee Keller Williams Hudson Valley

Light-filled home offering peace & serenity situated on a large, flat grassy lot. This warm home has many upgrades including new siding, almost new roof, many new windows, re-finished hardwood flooring, and more. Easy, one level living offers you a convenient layout with living room, dining room, two good size bedrooms, finished attic with extended living space(bedroom, office etc), unfinished

Silvana Milinovich RE/MAX Prime Properties

Discover the perfect blend of comfort and convenience in this delightful 3-bedroom, 1-bathroom ranch-style home located at 7 Manhattan Ave .This charming residence nestled on a quiet tree lined street offers a welcoming atmosphere and is ideal for both first-time buyers and those looking for an amazing value .The home has been maintained well by the owner and has many recent upgrades and updates

Darnell Williams R New York

Looking for a home you can make your own without breaking the bank? This 924 sq ft ranch style home on 4 private acres with direct Wallkill River access is a rare opportunity! This home needs some cleanup and finishing touches inside. You could move right in and update as you go! New Roof & New Septic, the big updates are already done. The Detached Garage needs a new roof and renovations.

Nancy LaBarbera Keller Williams Hudson Valley

Welcome to Your Catskills Retreat at 128 Kleis Road SpurTucked away on a quiet spur road and surrounded by evergreens, this charming single-level cabin blends cozy comfort with outdoor living.Relax on the spacious deck, soak in the private hot tub, or gather by the fire pit under the stars. Inside, enjoy an open layout with large windows, a stone fireplace, and sliders to the deck—perfect

Michelle Andzel Graziano Four Seasons Sotheby's International Realty

LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange

Richard Baxter Keller Williams Realty

Discover a rare mid-century contemporary set on just under an acre in Middletown. With more than 3,500 square feet, this 5 bedroom, 2 bath home offers incredible space, soaring ceilings, and floor-to-ceiling windows that fill every corner with natural light. The open, airy layout highlights the home’s architectural character, creating the perfect canvas for a modern makeover. The full basement

Kewin Garabito eXp Realty

Looking for something different? This spacious 4 bedroom 2 full bath contemporary raised ranch in the Town Of Wallkill just may be what you are looking for ! Open living room with cathedral ceilings & hardwood flooring. First floor primary bedroom & primary bath. Upper level has hardwood flooring through out with 3 bedrooms & a full bath. Family room on lower level. Rear deck overlooking your

Ernie Acampora River Realty Services, Inc.

Cute and cozy and very affordable; plus close to everything. This is a great starter or a downsizing home run. All original hardwood floors, large bathroom and a large rear deck leading to quiet back yard to play and relax. Brand new hot water heater, newer roof and windows, in addition this home has been freshly painted. Situated close to major highways, train station, shopping and restaurants

Tom Pahucki Keller Williams Realty

Don't miss out on this this 2-bedroom, 2.5-bath townhouse in the highly desirable Deer Run Condo community in Middletown, NY. This well-kept, two-floor unit features spacious bedrooms, large windows, a master bath, central air, and second floor laundry room. From the living door, you have a sliding glass door out to your Patio, perfect for comfortable living and easy entertaining. Enjoy access to

Chris Cardinal Keller Williams Realty

Elegant 2-Bedroom, 3-Bath End Unit in Sought-After Waters Edge Community Welcome to this beautifully maintained 2-bedroom, 2.5-bath end-unit condo in the desirable Waters Edge community—where comfort meets convenience in a peaceful, lakefront setting. Designed for easy living, this home offers a bright, open layout filled with natural light and modern charm. The first floor features a spacious

Jonathon Lee Keller Williams Hudson Valley

Move-in ready 3-bedroom, 2-bath townhouse in the Middletown School District. Home features new roof and siding (2023), new windows, and great flooring throughout. No repairs needed! Gas heat (no oil), fenced-in backyard, and covered porch. Delivered vacant at closing. Convenient location near schools, parks, shopping, and major routes. Perfect turnkey property for homeowner or investor!

Derek Greene Greene Realty Group

Beautiful Colonial Home located in one of the nicest neighborhoods in all of Middletown. This lovely home features a large sun-drenched Living room a brick Fireplace. Formal Dining Room, Very nice Kitchen with solid wood cabinetry and lots of countertop space. Second level offers a Tiled main bathroom. 3 VerySpacious bedrooms and plenty of closet space. Huge walk-up attic. Enclosed porch.

John Biasi Howard Hanna Rand Realty

WOW! Please check this beautiful end unit townhouse in the town of Wallkill with Goshen school district! This 3 bedrooms and 1.5 bathrooms house has almost everything brand new! New Roof, new flooring in the living room and dining are, new bathrooms, new carpet on the staircase through the hallway and the 3 bedrooms plus new hot water heater and new paved driveway for at least 6 cars! You will be

Anita S. Cristiano HomeSmart Homes & Estates

BACK ON MARKET: Your Dream Home Awaits at 28 Spring St, Middletown.Don't let this second chance slip away. This beautiful, 4 bedroom, 2 bathroom home is back on the market. Previous buyer's financing fell through. This is an incredible opportunity for you to step right in and secure a truly remarkable property. The seller has invested in significant updates to make this home move-in ready.

Leidy Placido Howard Hanna Rand Realty

Welcome to 14 Pennsylvania Avenue — a 3-bedroom, 1-bath ranch in the Minisink Valley School District offering convenient one-level living in a peaceful neighborhood setting. This solid home sits on a spacious 0.33-acre lot with a large, fenced-in backyard perfect for pets, play, or garden space. With good bones and a practical floor plan, it’s the perfect opportunity to bring your own style and

Dominick Tufano RE/MAX Benchmark Realty Group

CALLING ALL INVESTORS! This well-maintained two-family home in the heart of Middletown is a must-see opportunity! Each apartment offers two bedrooms, a spacious living room, a den/office and a full kitchen, perfect for tenants seeking comfort and convenience. Recent updates include a new roof, siding, soffits, and gutters—all completed within the past few months, ensuring peace of mind for years

Patricia Sassi RE/MAX Benchmark Realty Group

Discover this renovated colonial home nestled in the charming city of Middletown. This spacious single-family residence offers a perfect blend of classic charm and tasteful updates. The main level features a dedicated home office, an inviting living room, and an open-concept kitchen with stunning granite countertops and a center island. A formal dining room and a convenient half bath complete

Michael LaMorte Christie's Int. Real Estate

Welcome Home! Perfectly situated in one of Middletown’s most convenient locations, this beautifully updated 3-bedroom, 1.5-bath townhome offers comfort, style, and space all in one!Step inside to find a bright and welcoming entryway that opens to an updated kitchen featuring gleaming granite countertops, white cabinetry, modern appliances, and a convenient pantry. The formal dining room flows

Frank Muccari Cronin & Company Real Estate

Charming cape with water views on quiet street with boat launch! A total dream! House was recently renovated both inside and out. The recently painted rich, navy blue siding pops as you pull up alongside the newly built stone wall to welcome family and friends. The interior has been updated with new paint and flooring. Neutral colors and touches of shiplap throughout make the whole home very

Hilary Ryan Goldman Howard Hanna Rand Realty

A Truly Unique Opportunity – Live, Work, or Both!Welcome to a property that perfectly blends charm, function, and versatility. This special offering is not only a wonderful place to call home but also provides incredible potential to operate your own business—all in a convenient, easily accessible location.Currently configured as a single-family residence with mixed-use potential, this

Frank Muccari Cronin & Company Real Estate

Nestled in the sought-after Lake Ridge at Water’s Edge community in Middletown, NY, this beautifully maintained end-unit townhouse offers a perfect blend of comfort, style, and convenience. Featuring 2 bedrooms and 1.5 baths, the home boasts modern touches throughout, including luxury vinyl flooring, recessed LED lighting, and a cozy gas fireplace. The kitchen is equipped with stainless steel

Colin Seitz RE/MAX Benchmark Realty Group

Discover the potential in this charming 3-bedroom, 2-full-bath two-story home with 1,504 sq ft of living space. Full of character and solid construction, this property offers a formal dining room and plenty of room to grow with a full unfinished attic and full, unfinished, walk-out basement featuring washer/dryer hookups.Featuring strong bones and charming original touches, this home is

Vincent Reda Keller Williams Realty

Picked just for you is this adorable home on Apple Lane! From the moment you walk in, you’ll be greeted by a delightful blast from the past — knotty pine paneling, hardwood floors and an original kitchen complete with metal cabinets and whimsical upper metal cupboards with sliding glass doors that scream mid-century character. Whether you’re a fan of retro style or ready to put your modern touch

Patricia Sassi RE/MAX Benchmark Realty Group

Charming Corner Townhouse in Middletown – No HOA Fees!Welcome to 2 Riverdale Road, a delightful 3-bedroom, 1.5-bathroom townhouse nestled in the heart of Middletown, NY. This spacious 1,484 sq ft home offers a perfect blend of comfort and convenience, making it an ideal choice for families and first-time homebuyers.Key Features:Spacious Living: Enjoy the warmth of hardwood floors

Kilimanjaro Toussaint YourHomeSold Guaranteed Realty

A must see home! This beautiful colonial home will have everything brand new - from the exterior: roof, sidings, windows, porch, deck to the interior: kitchen, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, hardwood floorings - all NEW. Featuring 3

Anita S. Cristiano HomeSmart Homes & Estates